Startups usually fail, and there are already plenty of books & blogs & podcasts on how to succeed. I’ve personally helped build several early-stage startups, and I want to remember all the hard-learned lessons & constantly improve my decision-making process.

This won’t be very useful for anyone else, as I won’t publish the mapping of startup <-> lesson. That would be inappropriate, as some of these companies still exist, and in general it’s poor form to talk direct sh*t about former business partners.

I’ll only include observations from real startups (not side-projects) that I’ve personally worked for:

ChangeTrust

EarBuds

FeatherServe

Pool Cloud

Math Elf

CampusWatch

Walc

BaaS Bikes

Good Signals

Generate revenue in year 1

2+ engineers (I’m not a 1-man-band at the keyboard)

Very low expenses, no salaries

Bad Signals

Complicated monetization strategy

Product needs many users before it’s useful

Negative attitudes of any kind (my last developer was a crook, my last boss was a jerk, X is unfair, etc…)

My Common Pitfalls

Ego. I often assume that I posses some rare combination of skills, both abstract & concrete, that somehow perfectly align with this exact job, and I can’t easily delegate anything without a significant loss of quality. This is usually false, but I think that startups tend to attract personalities who are susceptible to this sort-of thing.

Tunnel-vision. Generally, managers at start-ups care a lot about the implementation details. This can have great benefits, but the loss is the ability to zoom out in the moment & calmly consider drastically different solutions to problems. I tend to get “stuck” on nuances, and I feel productive when I solve lots of little technical problems, even at the expense of higher-value tasks.

Burn-out. There is a whole toxic sub-culture of Gary-Vaynerchuks out there who promote unsustainable lifestyles that tightly couple self-worth to short-term productivity. Working long hours can be very helpful & is often necessary, but only after I’m confident that we’re building the correct thing. I’ve been really demoralized after sacrificing my work-life balance on a death-march to ship the wrong feature.

Lack of Conviction. I don’t think this one is present in canonical startup-advice, but I tend to communicate with everyone as I talk to fellow engineers, which means speaking with an accurate level of conviction, so as not to spread misinformation. I say “maybe”, “I think”, and usually discuss things I’m the least confident about in order to invite criticism & increase my understanding. However, most people tend to make sweeping statements, broad generalizations, and “probably-right” assertions with a big show of confidence, as it signals expertise, authority, and makes you sound smart. It can be frustrating to communicate with someone who is tuned to a different level of conviction, and I often forget to switch gears. I think this a serious character flaw of mine, and it creates real challenges because people hate it… I’ll work on it!

What I’m Great At

Building the initial product good, fast, and cheap (all 3)

Hiring great engineers that outlast me (the trick – I hire people that work with me, not for me)

Facilitating a fun atmosphere that makes work more interesting (usually)

What I Look for in a NonTechnical Founder

Success at a previous startup (the earlier they were, the better)

A unique channel-to-market, often achieved by cashing in on a career’s worth of relationship-equity to drive initial partnerships

Surprising Lessons

Mediocre / unhappy people are toxic, including myself when I’m unhappy

Fire fast AND Quit fast. The justifications for waiting are usually exaggerated in my head. I think all of us humans have this sense of loyalty, tribalism, or at least obligation that comes into play & causes us to stick with sub-optimal situations for longer than we should. Counter-intuitively, I’ve found that acting quickly is usually the more honest, compassionate approach anyways.